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GB2470338A - Process for the preparation of 4-(4-hydroxphenyl)but any-one using solid acid clay catalyst - Google Patents

Process for the preparation of 4-(4-hydroxphenyl)but any-one using solid acid clay catalyst Download PDF

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Publication number
GB2470338A
GB2470338A GB1016235A GB201016235A GB2470338A GB 2470338 A GB2470338 A GB 2470338A GB 1016235 A GB1016235 A GB 1016235A GB 201016235 A GB201016235 A GB 201016235A GB 2470338 A GB2470338 A GB 2470338A
Authority
GB
United Kingdom
Prior art keywords
range
hours
montmorillonite clay
acid
solid acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB1016235A
Other versions
GB2470338B (en
GB201016235D0 (en
Inventor
Dipak Kumar Dutta
Madan Gopal Patha
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Council of Scientific and Industrial Research CSIR
Original Assignee
Council of Scientific and Industrial Research CSIR
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Council of Scientific and Industrial Research CSIR filed Critical Council of Scientific and Industrial Research CSIR
Publication of GB201016235D0 publication Critical patent/GB201016235D0/en
Publication of GB2470338A publication Critical patent/GB2470338A/en
Application granted granted Critical
Publication of GB2470338B publication Critical patent/GB2470338B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/16—Clays or other mineral silicates
    • B01J35/002—
    • B01J35/1019—
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/633—Pore volume less than 0.5 ml/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/635—0.5-1.0 ml/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/06—Washing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/30—Ion-exchange
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Solid acid catalyst such as acid activated-Montmorillonite clay composite has been developed by modifying the Na-Montmorillonite clay with acid (HC1) treatment for different periods such as 5 minutes to about 4 hours and activating at about 120°C for about 2 hours. Friedel Crafts alkylation reaction between phenol and 4-hydroxybutan-2-one in presence of the acid activated Montmorillonite clay catalysts exhibiting layered clay structures (basal spacing d001ranging from about 10 to 13.5 Å), high surface area (250 - 400 m2/g), highly porous {micropores in the range 5 to 15 Å and mesopores in the range 30 to 80 Å}, average pore volume 0.2 to 0.65 cc/g, and surface acidity in the range 0.4 - 0.6 mmol/g; under constant stirring and at pressure of 1-15 bar, temperature 100 - 150°C for a period of about 12 - 24 hours produces 4-(4-hydroxyphenyl)butan-2-one (Raspberry ketone) exlubiting conversion about 35 - 55 % and high selectivity in the range 75 - 81 %.
GB1016235.2A 2008-03-26 2009-03-16 Process for the preparation of 4-(4-hydroxyphenyl)butan-2-one using solid acid clay catalyst Expired - Fee Related GB2470338B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN772DE2008 2008-03-26
PCT/IN2009/000178 WO2009118755A2 (en) 2008-03-26 2009-03-16 Process for the preparation of 4-(4-hydroxyphenyl)butan-2-one using solid acid clay catalyst

Publications (3)

Publication Number Publication Date
GB201016235D0 GB201016235D0 (en) 2010-11-10
GB2470338A true GB2470338A (en) 2010-11-17
GB2470338B GB2470338B (en) 2013-03-13

Family

ID=40903381

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1016235.2A Expired - Fee Related GB2470338B (en) 2008-03-26 2009-03-16 Process for the preparation of 4-(4-hydroxyphenyl)butan-2-one using solid acid clay catalyst

Country Status (4)

Country Link
US (1) US8471068B2 (en)
CA (1) CA2719274C (en)
GB (1) GB2470338B (en)
WO (1) WO2009118755A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102372617A (en) * 2011-11-09 2012-03-14 山东新和成药业有限公司 Preparation method of spice 4-(4-hydroxyphenyl)-2-butanone
CN108530280A (en) * 2018-05-21 2018-09-14 浙江工业大学 The method of acid immobilized ionic liquid-catalyzed synthesis raspberry ketone
CN110801847A (en) * 2018-08-06 2020-02-18 泰兴金江化学工业有限公司 Method for preparing acetate from clay-based solid acid
WO2021152214A1 (en) * 2020-01-29 2021-08-05 Koivubiotech Oy Composition comprising raspberry ketone
FR3116819B1 (en) 2020-12-01 2023-11-17 Rhodia Operations Process for preparing frambinone

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014530A1 (en) * 1993-11-24 1995-06-01 Laporte Industries Limited Catalytic materials
EP0702596B1 (en) * 1993-06-10 1996-12-18 Laporte Industries Limited Catalytic materials comprising layered clay macrospheres

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2729386B1 (en) 1995-01-12 1997-04-04 Robertet Sa PROCESS FOR THE PREPARATION OF BUTANONE DERIVATIVES
JP2005255419A (en) * 2004-03-09 2005-09-22 Kuraray Co Ltd Palladium-bimetal cation exchange montmorillonite and uses thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0702596B1 (en) * 1993-06-10 1996-12-18 Laporte Industries Limited Catalytic materials comprising layered clay macrospheres
WO1995014530A1 (en) * 1993-11-24 1995-06-01 Laporte Industries Limited Catalytic materials

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. of Org. Chem., American Chemical Society, 1994, Vo.59(20), Tateiwa J-I et. al., pages 5901-5904. *
Langmuir, 1986, Vol.3(5), Mendioroz S. et.al., pages 676-681. *

Also Published As

Publication number Publication date
GB2470338B (en) 2013-03-13
CA2719274A1 (en) 2009-10-01
WO2009118755A3 (en) 2009-12-03
GB201016235D0 (en) 2010-11-10
WO2009118755A2 (en) 2009-10-01
US20110257439A1 (en) 2011-10-20
WO2009118755A8 (en) 2011-08-04
CA2719274C (en) 2015-12-29
US8471068B2 (en) 2013-06-25

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PCNP Patent ceased through non-payment of renewal fee

Effective date: 20180316